Microwave-assisted synthesis of some hybrid molecules containing penicillanic acid or cephalosporanic acid moieties and investigation of their biological activities

Alpay Karaoglu, Sengul/0000-0003-1047-8350WOS: 000334184400039Ethyl 4-amino-2-fluorophenylpiperazin-1-carboxylates containing a 1,3-oxazol(idin)e, 5-thioxo-1,2,4-triazole, 1,3,4-thiadiazole, 5-thioxo-1,3,4-oxadiazole, or 1,3-thiazole nucleus were obtained starting from ethyl piperazine-1-carboxylate (1) by several steps. the treatment of amine, 3 or hydrazide, 9 with several aromatic aldehydes generated the corresponding arylmethyleneamino (3a-f) or arylidenehydrazino (12a-c) compounds. the Mannich reaction between the 1,2,4-triazole or 1,3,4-oxadiazole compounds and 7-aca produced cephalosporanic acid derivatives. Penicillanic acid derivatives were obtained when 6-apa was used in the Mannich reactions. the synthesized compounds were screened for their antimicrobial, antilipase, and antiurease activities. Some of them were found to possess good-moderate antimicrobial activity against the test microorganisms. Two compounds exhibited antiurease activity, and four of them displayed antilipase activity.Scientific and Technological Research Council of Turkey (TUBITAK)Turkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [107T333]; Karadeniz Technical University, BAP, TurkeyKaradeniz Technical University [8623]This Project was supported by Scientific and Technological Research Council of Turkey (TUBITAK, Project No: 107T333) and Karadeniz Technical University, BAP, Turkey (Ref. No. 8623) and is gratefully acknowledged

Microwave-assisted synthesis of some hybrid molecules derived from morpholine and investigation of their antimicrobial activities

2H-1,2,4-triazol-3(4H)-one compound was obtained starting from 4-(2-fluoro-4-nitrophenyl)morpholine via several steps. Then, these compounds were converted to the corresponding fluoroquinolone hybrids via one pot three component Mannich reaction. Moreover, the synthesis of eleven compounds, which can be considered as conazole analogues, was performed starting from 1,2,4-triazole-3-one compounds via three steps by either conventional or microwave mediated conditions. The effect of different solvents and microwave power on microwave prompted reactions was examined as well

Antimicrobial and antiurease activities of newly synthesized morpholine derivatives containing an azole nucleus

2-[6-(Morpholin-4-yl)pyridin-3-ylamino]acetohydrazide (4) was obtained starting from 6-morpholin-4-ylpyridin-3-amine (2) via the formation of ester (3) and then converted to the corresponding Schiff bases (5, 6) with the reaction with aromatic aldehydes. The carbothioamide (9), obtained from the reaction of hydrazide with phenylisothiocyanate, was converted to the corresponding 1,2,4-triazole (11) and 1,3,4-thiadiazole (12) derivatives by the treatment with NaOH or H2SO4, respectively. The cyclocondenzation of 9 with 4-chlorophenacyl bromide or ethyl bromoacetate produced the corresponding 1,3-thiazole (10) or 1,3-thiazolidine derivatives (13), respectively. Antimicrobial and antiurease activities of newly synthesized compounds were investigated. Some of them were found to be active on M. smegmatis, and they displayed activity toward C. albicans and S. cerevisiae in high concentration. Compound 10 proved to be the most potent showing an enzyme inhibition activity with an IC50 = 2.37 +/- A 0.19 mu M

Antimicrobial, antioxidant and antiproliferative activities of novel quinolones

The compound (2) formed by esterification of dimethyl morpholine (1) was converted to acetohydrazide (3). Subsequently Schiff bases (4 a-d) and carboxy(thio)amide derivatives (5 a-e) were synthesized. Then 1,2,4-triazole (6 a-e), thia(oxa)zolidine (7 c,e) and thia(oxa)zol (8 c,e) derivatives were obtained by ring closure from carboxy(thio)amides. Mannich bases, which are containing quinolone were synthesized from 1,2,4-triazoles. The structures of newly synthesized compounds were illuminated by spectroscopic methods. Their antimicrobial (MIC method), antioxidant (DPPH, FRAP, and CUPRAC methods), and anticancer activities (MTT method) were examined. Results showed that most of the compounds exhibited good antimicrobial (<0.03-31.25 mu g/mL with MIC values) and antioxidant activities (IC50=0.001-0.004 with DPPH values). Also, some of the compounds have been found to have antiproliferative effects on the prostate (PC-3), liver (Hep3B), and breast (MCF-7) human cancer cells, and also these compounds did not have a cytotoxic effect on a normal cell.This work was supported by Artvin Coruh University, BAP (2016.F11.02.06), Turkey

Microwave-assisted and conventional synthesis of novel antimicrobial 1,2,4-triazole derivatives containing nalidixic acid skeleton

Carbothioamides 4a,b, obtained from nalidixic acid, were converted to the corresponding 1,3-thiazolidine derivatives 5a,b by cyclocondensation with 2-bromo-1-(4-chlorophenyl)ethanone. Treatment of 4a,b with base afforded 1,2,4-triazoles 6a,b. The synthesis of 1,3-oxazolidine 7 was performed by the reaction of compound 4a with ethyl bromoacetate. Treatment of 4a with acid produced 1,3,4-thiadiazole 8. The reaction of compounds 6a and 6b with several heterocyclic amines in the presence of formaldehyde gave the corresponding Mannich bases 9–15 containing various pharmacophore groups. Conventional and microwave-assisted methods were used for the synthesis. The effect of an acid catalyst on Mannich reactions was investigated. The structures of the newly synthesized compounds were elucidated on the basis of 1H NMR, 13C NMR, FTIR, EIMS techniques, and elemental analysis. All compounds were screened for their antimicrobial activity

Synthesis of Novel 4-Alkylidene-and 4-Alkylamino-5-oxo-4,5-Dihydro-[1,2,4]triazole Derivatives and Investigation of Their Antitumor Activities

tive reduction of compounds 6a-e and 7b-e with NaBH4. The in vitro antitumor activity of some selected compounds was screened by the National Cancer Institute (USA) against several human tumor cell lines, and compounds 8c, 9d and 11c were found to be active

Synthesis and antimicrobial activities of 2-(5-mercapto)- 1,3-oxadiazol-2-ylmethyl-1,2,4-triazol-3-one derivatives

The synthesis of 4-amino-2-[(5-mercapto-1,3,4-oxadiazol-2-yl)methyl]-5-(4-methylphenyl)-2,4-dihydro-3H - 1,2,4-triazol-3-one (2) and 4-amino-2-[(4-amino-5-mercapto-4H -1,2,4-triazol-3-yl)methyl]-5-(4-methylphenyl)- 2,4-dihydro-3H -1,2,4-triazol-3-one (5) was performed starting from 2-[4-amino-3-(4-methylphenyl)-5-oxo- 4,5-dihydro-1H -1,2,4-triazol-1-yl]acetohydrazide (1). The treatment of 2 and 5 with 4-fluorobenzaldehyde (for 8) or salicylaldehyde (for 6) afforded the corresponding Schiff bases (6 and 8). The condensation of 5 with phenacyl bromide produced 4-amino-5-(4-methylphenyl)-2-[(6-phenyl-7H-[1,2,4]triazolo[3,4- b][1,3,4]thiadiazin-3-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (7). The alkylation of 2 and 8 was carried out by using methyl iodide in basic media. Compounds 3 and 10a,b were prepared by aminoalkylation of 2 and 8 with 4-fluorophenyl piperazine, morpholine, or 4-methyl piperazine in the presence of formaldehyde. The synthesized compounds were screened for their antimicrobial activities and, with the exception of 2, 4, 7, and 9, were found to possess good or moderate activities against the screened bacterial strains except Candida tropicalis and Candida albicans

Design, synthesis and biological activities of some 7-aminocephalosporanic acid derivatives

Alpay Karaoglu, Sengul/0000-0003-1047-8350WOS: 000330603900059PubMed: 24095755The treatment of 7-ACA with 4-substituted benzensulfonyl chlorides afforded the compounds containing 4-nitro/aminophenyl sulfonylamino moiety in the cephalosporanic acid skeleton (2, 4). the synthesis of the cephalosporanic acid derivatives containing 1,3-thiazole or 5-oxo-1,3-thiazolidine nucleus and sulfonamide function (8a, 8b, 10) was performed starting from 7-ACA by several steps. the reaction of 7ACA with [4-(2-fluoro-4-nitrophenyl)piperazin-1-yl]acetyl chloride afforded the corresponding 7{[4-(2-fluoro-4-nitrophenyl)piperazin-1-yl]acetyl)amino derivative (13). the synthesized compounds were screened for their antimicrobial and antiurease activities. Some of them were found to possess good moderate antimicrobial activity against the test microorganisms. Compound 5d was observed to have moderate anti-urease activity. (C) 2013 Elsevier Masson SAS. All rights reserved.Scientific and Technological Research Council of Turkey (TUBITAK)Turkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [111T427]The support provided by Scientific and Technological Research Council of Turkey (TUBITAK, Project no: 111T427)

Synthesis and antimicrobial activities of some new biheterocyclic compounds containing 1,2,4-triazol-3-one and 1,3,4-thiadiazole moieties

WOS: 0002807370000042-(4-Amino-3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-N'-[(2,6-dihalogenophenyl)methylene]acetohydrazides (3a, b) was obtained via the formation of 2-(4-amino-3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl) acetohydrazide (2), which was obtained starting from 4-amino-5-(4-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (1) in 2 steps. 2-{[ 4-amino-3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl] acetyl}-N-phenylhydra-zine carbothioamide (4), which was prepared starting from 2, was converted to the corresponding 1,3,4-thiadiazole derivative (5) in acidic media. Moreover, the basic treatment of 4 resulted in the formation of 4-amino-5-(4-chlorophenyl)-2-[(4-phenyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl) methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (7). The reactions of compounds 5 and 7 with methyl iodide in the presence of sodium ethoxide afforded the corresponding N-methyl (6) and S-methyl (8) derivatives, respectively. The synthesis of Mannich bases (10a and 10b) was performed from the reaction of 7 with morpholine or piperazine in the presence of formaldehyde. All the newly synthesized compounds were screened for their antimicrobial activity. The antimicrobial activity study revealed that compounds 3a, 3b, and 5 showed good antimicrobial activities against the test microorganisms as compared with ampicillin.Scientific and Technological Research Council of Turkey (TUBITAK)Turkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [107T333]This work supported by the Scientific and Technological Research Council of Turkey (TUBITAK, Project no: 107T333)

Synthesis of novel Schiff bases using green chemistry techniques; antimicrobial, antioxidant, antiurease activity screening and molecular docking studies

Schiff base derivatives were synthesized in this study via conventional, microwave irradiation and ultrasound sonication methods. Optimization conditions were examined for several parameter such as solvent, reaction time and yield. After determining the optimization conditions, the compounds were synthesized by using ultrasound sonication. The structures of the synthesized compounds were examined by spectral data, and the antiurease, antioxidant and antimicrobial activities of the Schiff bases derivatives were investigated due to the imine group (-C=N-) and promising results were obtained. The enzyme inhibitory potentials of these compounds were further validated through molecular docking studies. Also, In Silico ADME prediction studies were calculated for compounds